#------------------------------------------------------------------------------
#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/25/7112500.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7112500
loop_
_publ_author_name
'Ciupa, Alexander'
'De Bank, Paul A.'
'Mahon, Mary F.'
'Wood, Pauline J.'
'Caggiano, Lorenzo'
_publ_section_title
;
 Synthesis and antiproliferative activity of some
 3-(pyrid-2-yl)-pyrazolines
;
_journal_issue                   6
_journal_name_full               MedChemComm
_journal_page_first              956
_journal_paper_doi               10.1039/c3md00077j
_journal_volume                  4
_journal_year                    2013
_chemical_formula_sum            'C15 H14 N4 S'
_chemical_formula_weight         282.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.768(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7950(2)
_cell_length_b                   14.7280(3)
_cell_length_c                   10.0360(2)
_cell_measurement_reflns_used    14347
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     1378.74(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV 1997-2004)'
_computing_data_reduction        'Denzo & Scalepack (Otwinowski, Minor 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97/2 (Sheldrick 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24456
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         3.52
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            block
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       colorless
_exptl_crystal_F_000             592
_exptl_crystal_size_max          .35
_exptl_crystal_size_mid          .35
_exptl_crystal_size_min          .12
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3152
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0439P)²+0.4856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                2385
_reflns_number_total             3152
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3md00077j.txt
_cod_data_source_block           k10farm2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7112500
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.46282(4) 0.17783(3) 1.07454(4) 0.03050(14) Uani 1 1 d .
N1 N 0.23668(15) 0.24736(10) 0.88053(15) 0.0291(3) Uani 1 1 d D
N2 N 0.45409(13) 0.27819(9) 0.85211(13) 0.0214(3) Uani 1 1 d .
N3 N 0.38110(13) 0.32553(8) 0.73077(13) 0.0205(3) Uani 1 1 d .
N4 N 0.48978(14) 0.35498(9) 0.43074(13) 0.0235(3) Uani 1 1 d .
C1 C 0.37905(16) 0.23688(10) 0.92880(16) 0.0219(3) Uani 1 1 d .
C2 C 0.60912(15) 0.27330(10) 0.87030(16) 0.0205(3) Uani 1 1 d .
H2 H 0.6473 0.2117 0.9040 0.025 Uiso 1 1 calc R
C3 C 0.69237(16) 0.34632(10) 0.96889(16) 0.0207(3) Uani 1 1 d .
C4 C 0.62794(18) 0.40475(11) 1.03987(16) 0.0268(4) Uani 1 1 d .
H4 H 0.5280 0.3999 1.0268 0.032 Uiso 1 1 calc R
C5 C 0.7078(2) 0.47040(13) 1.12989(18) 0.0349(4) Uani 1 1 d .
H5 H 0.6621 0.5101 1.1775 0.042 Uiso 1 1 calc R
C6 C 0.8530(2) 0.47811(13) 1.1503(2) 0.0389(5) Uani 1 1 d .
H6 H 0.9078 0.5224 1.2130 0.047 Uiso 1 1 calc R
C7 C 0.91851(19) 0.42095(12) 1.0789(2) 0.0357(4) Uani 1 1 d .
H7 H 1.0184 0.4264 1.0918 0.043 Uiso 1 1 calc R
C8 C 0.83876(17) 0.35582(11) 0.98865(18) 0.0273(4) Uani 1 1 d .
H8 H 0.8845 0.3171 0.9396 0.033 Uiso 1 1 calc R
C9 C 0.61005(16) 0.28849(11) 0.71863(16) 0.0220(3) Uani 1 1 d .
H9A H 0.6905 0.3280 0.7147 0.026 Uiso 1 1 calc R
H9B H 0.6150 0.2303 0.6708 0.026 Uiso 1 1 calc R
C10 C 0.46755(15) 0.33459(10) 0.65744(15) 0.0187(3) Uani 1 1 d .
C11 C 0.41951(15) 0.37995(10) 0.52084(15) 0.0186(3) Uani 1 1 d .
C12 C 0.44274(18) 0.38974(11) 0.30101(17) 0.0279(4) Uani 1 1 d .
H12 H 0.4889 0.3712 0.2349 0.033 Uiso 1 1 calc R
C13 C 0.33097(18) 0.45098(11) 0.25817(17) 0.0277(4) Uani 1 1 d .
H13 H 0.3018 0.4739 0.1653 0.033 Uiso 1 1 calc R
C14 C 0.26263(17) 0.47816(11) 0.35308(17) 0.0266(4) Uani 1 1 d .
H14 H 0.1868 0.5212 0.3272 0.032 Uiso 1 1 calc R
C15 C 0.30629(16) 0.44174(10) 0.48662(17) 0.0236(3) Uani 1 1 d .
H15 H 0.2601 0.4585 0.5535 0.028 Uiso 1 1 calc R
H1A H 0.1791(19) 0.2159(13) 0.930(2) 0.055(6) Uiso 1 1 d D
H1B H 0.1915(19) 0.2747(13) 0.7894(11) 0.047(6) Uiso 1 1 d D
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 H1A 117.5(13)
C1 N1 H1B 120.9(12)
H1A N1 H1B 120.4(17)
C1 N2 N3 119.73(12)
C1 N2 C2 128.48(13)
N3 N2 C2 111.48(11)
C10 N3 N2 107.42(12)
C12 N4 C11 116.95(14)
N1 C1 N2 115.29(14)
N1 C1 S1 123.48(12)
N2 C1 S1 121.23(12)
N2 C2 C3 111.95(12)
N2 C2 C9 100.77(11)
C3 C2 C9 112.13(12)
N2 C2 H2 110.5
C3 C2 H2 110.5
C9 C2 H2 110.5
C4 C3 C8 118.34(15)
C4 C3 C2 122.43(14)
C8 C3 C2 119.23(14)
C3 C4 C5 120.80(16)
C3 C4 H4 119.6
C5 C4 H4 119.6
C6 C5 C4 120.29(17)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C7 119.55(17)
C5 C6 H6 120.2
C7 C6 H6 120.2
C6 C7 C8 120.13(16)
C6 C7 H7 119.9
C8 C7 H7 119.9
C7 C8 C3 120.87(16)
C7 C8 H8 119.6
C3 C8 H8 119.6
C10 C9 C2 100.62(12)
C10 C9 H9A 111.6
C2 C9 H9A 111.6
C10 C9 H9B 111.6
C2 C9 H9B 111.6
H9A C9 H9B 109.4
N3 C10 C11 120.14(13)
N3 C10 C9 114.21(13)
C11 C10 C9 125.44(13)
N4 C11 C15 123.04(14)
N4 C11 C10 114.83(13)
C15 C11 C10 122.10(13)
N4 C12 C13 123.73(15)
N4 C12 H12 118.1
C13 C12 H12 118.1
C14 C13 C12 118.66(15)
C14 C13 H13 120.7
C12 C13 H13 120.7
C13 C14 C15 118.96(15)
C13 C14 H14 120.5
C15 C14 H14 120.5
C14 C15 C11 118.60(14)
C14 C15 H15 120.7
C11 C15 H15 120.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.6842(16)
N1 C1 1.338(2)
N1 H1A 0.974(5)
N1 H1B 0.974(5)
N2 C1 1.359(2)
N2 N3 1.3960(17)
N2 C2 1.4748(19)
N3 C10 1.2871(19)
N4 C12 1.343(2)
N4 C11 1.3441(19)
C2 C3 1.519(2)
C2 C9 1.541(2)
C2 H2 1.0000
C3 C4 1.386(2)
C3 C8 1.393(2)
C4 C5 1.390(2)
C4 H4 0.9500
C5 C6 1.379(3)
C5 H5 0.9500
C6 C7 1.384(3)
C6 H6 0.9500
C7 C8 1.385(2)
C7 H7 0.9500
C8 H8 0.9500
C9 C10 1.504(2)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.468(2)
C11 C15 1.394(2)
C12 C13 1.382(2)
C12 H12 0.9500
C13 C14 1.380(2)
C13 H13 0.9500
C14 C15 1.385(2)
C14 H14 0.9500
C15 H15 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C1 N2 N3 C10 -161.42(14)
C2 N2 N3 C10 12.75(16)
N3 N2 C1 N1 -1.3(2)
C2 N2 C1 N1 -174.40(14)
N3 N2 C1 S1 179.10(11)
C2 N2 C1 S1 6.0(2)
C1 N2 C2 C3 -89.28(18)
N3 N2 C2 C3 97.19(14)
C1 N2 C2 C9 151.37(15)
N3 N2 C2 C9 -22.16(15)
N2 C2 C3 C4 4.7(2)
C9 C2 C3 C4 117.11(16)
N2 C2 C3 C8 -174.87(13)
C9 C2 C3 C8 -62.45(18)
C8 C3 C4 C5 -0.8(2)
C2 C3 C4 C5 179.62(15)
C3 C4 C5 C6 -0.3(3)
C4 C5 C6 C7 1.0(3)
C5 C6 C7 C8 -0.7(3)
C6 C7 C8 C3 -0.4(3)
C4 C3 C8 C7 1.1(2)
C2 C3 C8 C7 -179.28(15)
N2 C2 C9 C10 21.41(14)
C3 C2 C9 C10 -97.81(14)
N2 N3 C10 C11 178.38(12)
N2 N3 C10 C9 3.42(17)
C2 C9 C10 N3 -16.74(16)
C2 C9 C10 C11 168.61(13)
C12 N4 C11 C15 -2.5(2)
C12 N4 C11 C10 175.33(13)
N3 C10 C11 N4 -154.21(14)
C9 C10 C11 N4 20.1(2)
N3 C10 C11 C15 23.7(2)
C9 C10 C11 C15 -161.97(14)
C11 N4 C12 C13 2.2(2)
N4 C12 C13 C14 -0.3(3)
C12 C13 C14 C15 -1.4(2)
C13 C14 C15 C11 1.0(2)
N4 C11 C15 C14 1.0(2)
C10 C11 C15 C14 -176.75(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 90666569
